In the end, we had three parties in the same weekend that were interested so we actually got to choose the tenant with the most desirable tenant credentials.

I am realistic about prices in these neighborhoods, but still desire a minimum of $100 in cash flow per unit when I eventually move out.  

Some options to consider might be owner financing or lease option.I would still make an offer to wholesale, and gauge her reaction.If you don't have the cash for owner financing, and must wholesale or nothing at all, I would call her in a month or two to gauge her desire to sell.In my opinion, she would like to sell, but she doesn't feel like she must sell.  

I would still want something in writing if possible but all things considered if the above is true then yes, this is a much more desirable and I can see value here.  

Any repairs or clogs during the lease are the responsibility of the tenant.Wouldn't that take the potential economic risk off the landlord while giving the tenant something many desire?

The tenant is a long-term tenant and the seller lives out of state, and so thought they could do anything with the property they desired.

If we can't counsel with sellers, eye to eye or ear to ear, our chances are less in creating that desired profit. 

After talking to him a little more, we realized his actual desire was to pull some money out of the building to invest elsewhere but was worried about the appraisal and state of the building.

Here's how I see your deal:Gross rents: $5,400Operating Expenses: $2,700NOI: $2,700Less Desired Cash Flow: $1,200Money Available for Mortgage Payment (P & I only): $1,500Putting that in a mortgage calculator with a 30 yr term and 7% interest rate, that gives the maximum purchase price $225,461 (less any repairs needed).Good Luck,Mike

Invest if you desire and write down clear expectations too.